Synthesis and inhibitory evaluation of cyclohexen-2-yl- and cyclohexyl-substituted phenols and quinones to endothelial cell and cancer cells.

Abstract

Alkylation of phenols with 1,3-cyclohexadiene (1) has been conducted and a series of cyclohexen-2-yl- and cyclohexyl-substituted phenols and quinones were screened against the proliferation of HUVEC and cancer cells. Phenol type as well as the size and occupied position of the substitute are important for the alkylating reaction and the inhibitory activity and selectivity of a compound. 2,5-di(cyclohexen-2-yl)benzene-1,4-diol (25) bearing two cyclohexen-2-yl groups and 2-tert-butyl-5-(cyclohexen-2-yl)benzene-1,4-diol (30) bearing cyclohexen-2-yl and tert-butyl groups exhibited good selectivity against HUVEC proliferation (IC50s of 2.0 and 1.4 microM, respectively) with relatively low toxicity to ccc-HPF-1.

• Authors: Xin Liu, Yingyong Ou, Shaopeng Chen, Xin Lu, Hao Cheng, Xian Jia, Decai Wang, Guo-Chun Zhou
• Journal: European journal of medicinal chemistry (Eur J Med Chem) Vol. 45 Issue 6 Pg. 2147-53 (Jun 2010) ISSN: 1768-3254 [Electronic] France
• PMID: 20149494 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright (c) 2010 Elsevier Masson SAS. All rights reserved.

Chemical References

• Cyclohexanes
• Cyclohexenes
• Phenols
• Quinones
• cyclohexene
• Cyclohexane
• 1,3-cyclohexadiene

Topics

• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Cyclohexanes (chemistry)
• Cyclohexenes (chemistry)
• Endothelial Cells (cytology, drug effects)
• Humans
• Inhibitory Concentration 50
• Phenols (chemical synthesis, chemistry, pharmacology)
• Quinones (chemical synthesis, chemistry, pharmacology)
• Structure-Activity Relationship